#------------------------------------------------------------------------------ #$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301806 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238889.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2238889 loop_ _publ_author_name 'Zhong, Kai-Long' _publ_section_title ; 2,9-Dimethyl-1,10-phenanthrolin-1-ium 2,4,5-tricarboxybenzoate monohydrate ; _journal_coeditor_code LH5664 _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1782 _journal_page_last o1783 _journal_paper_doi 10.1107/S1600536813030857 _journal_volume 69 _journal_year 2013 _chemical_formula_moiety 'C14 H13 N2 +, C10 H5 O8 -, H2 O' _chemical_formula_sum 'C24 H20 N2 O9' _chemical_formula_weight 480.42 _chemical_name_systematic ; 2,9-Dimethyl-1,10-phenanthrolin-1-ium 2,4,5-tricarboxybenzoate monohydrate ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL- _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 7.1135(8) _cell_length_b 19.4512(11) _cell_length_c 30.800(2) _cell_measurement_reflns_used 2016 _cell_measurement_temperature 223.15 _cell_measurement_theta_max 25.9570 _cell_measurement_theta_min 3.3610 _cell_volume 4261.7(6) _computing_cell_refinement 'CrystalClear (Rigaku, 2007)' _computing_data_collection 'CrystalClear (Rigaku, 2007)' _computing_data_reduction 'CrystalClear (Rigaku, 2007)' _computing_molecular_graphics ; SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008) ; _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 223.15 _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1725 _diffrn_reflns_av_sigmaI/netI 0.1007 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 19580 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.88 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.46781 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(REQAB; Jacobson, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2000 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.368 _refine_diff_density_min -0.404 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 316 _refine_ls_number_reflns 4346 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.001 _refine_ls_R_factor_all 0.1489 _refine_ls_R_factor_gt 0.0881 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1341P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2192 _refine_ls_wR_factor_ref 0.2719 _reflns_number_gt 2278 _reflns_number_total 4346 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL KL in Pbca CELL 0.71073 7.1135 19.4512 30.8000 90.000 90.000 90.000 ZERR 8 0.0008 0.0011 0.0020 0.000 0.000 0.000 LATT 1 SYMM 0.50000 - X , - Y , 0.50000 + Z SYMM 0.50000 + X , 0.50000 - Y , - Z SYMM - X , 0.50000 + Y , 0.50000 - Z SFAC C H N O UNIT 192 160 16 72 L.S. 7 SIZE 0.15 0.20 0.35 DFIX 0.82 0.001 O1W H1WA O1W H1WB DFIX 1.35 0.01 H1WA H1WB FMAP 2 PLAN 5 EQIV $1 1/2-X, Y+1/2, Z EQIV $2 X+1/2, -Y+1/2, -Z EQIV $3 X-1/2, Y, 1/2-Z EQIV $4 X+1, Y , Z HTAB O2 O3 HTAB O5 O1_$1 HTAB O5 O2_$1 HTAB O8 O3_$2 HTAB N1 O1W_$3 HTAB O1W O4_$2 HTAB O1W O7_$4 ACTA BOND $H CONF WGHT 0.134100 FVAR 0.09640 O1 4 0.274854 0.087528 0.048976 11.00000 0.11876 0.02120 = 0.04603 -0.00035 -0.00277 0.00772 O1W 4 0.904525 0.172625 0.150478 11.00000 0.10729 0.06632 = 0.05821 0.01996 -0.02336 -0.03666 AFIX 3 H1WA 2 0.832145 0.186275 0.131638 11.00000 -1.50000 H1WB 2 0.973235 0.203935 0.158598 11.00000 -1.50000 AFIX 0 O2 4 0.196357 0.094314 -0.019235 11.00000 0.13077 0.03011 = 0.04518 -0.00947 -0.01614 0.00464 AFIX 83 H2 2 0.166943 0.123947 -0.036910 11.00000 -1.50000 AFIX 0 O3 4 0.145304 0.180815 -0.073319 11.00000 0.07667 0.03589 = 0.04164 -0.00856 -0.01078 0.00438 O4 4 0.182782 0.292653 -0.081310 11.00000 0.09502 0.04079 = 0.04637 0.00123 -0.00437 -0.00266 O5 4 0.194596 0.455767 0.025613 11.00000 0.14916 0.01805 = 0.04576 0.00328 -0.00217 -0.00498 AFIX 83 H5 2 0.194096 0.495769 0.034014 11.00000 -1.50000 AFIX 0 O6 4 0.196065 0.434545 0.095470 11.00000 0.17078 0.03060 = 0.04270 -0.00688 -0.00024 0.00460 O7 4 0.112856 0.299088 0.152989 11.00000 0.07517 0.04922 = 0.04652 -0.00759 0.01862 -0.00685 O8 4 0.409357 0.321755 0.139652 11.00000 0.07190 0.04892 = 0.03707 -0.00678 -0.00021 -0.00536 AFIX 83 H8 2 0.481198 0.320335 0.118851 11.00000 -1.50000 AFIX 0 N1 3 0.334801 0.040667 0.323087 11.00000 0.05382 0.02784 = 0.04371 0.00348 0.00082 0.00221 AFIX 43 H1A 2 0.375637 0.082013 0.326071 11.00000 -1.20000 AFIX 0 N2 3 0.426920 0.121651 0.253350 11.00000 0.04810 0.02609 = 0.04206 0.00030 -0.00069 0.00365 C1 1 0.296777 0.004380 0.359058 11.00000 0.05653 0.04229 = 0.05274 0.01296 -0.00059 0.00337 C2 1 0.229802 -0.062842 0.353677 11.00000 0.05856 0.03996 = 0.07112 0.02168 0.00628 0.00535 AFIX 43 H2B 2 0.201819 -0.089226 0.378015 11.00000 -1.20000 AFIX 0 C3 1 0.205120 -0.090062 0.313447 11.00000 0.05158 0.03304 = 0.07750 0.00868 0.00907 0.00281 AFIX 43 H3A 2 0.160792 -0.134826 0.310665 11.00000 -1.20000 AFIX 0 C4 1 0.245654 -0.051508 0.275922 11.00000 0.04294 0.02829 = 0.06783 0.00293 0.00122 0.00231 C5 1 0.220470 -0.076985 0.232798 11.00000 0.04557 0.03038 = 0.07710 -0.01363 -0.00318 -0.00546 AFIX 43 H5A 2 0.179247 -0.121843 0.228490 11.00000 -1.20000 AFIX 0 C6 1 0.255883 -0.036647 0.198606 11.00000 0.05093 0.04269 = 0.05582 -0.01595 -0.00097 0.00243 AFIX 43 H6A 2 0.235365 -0.053948 0.170860 11.00000 -1.20000 AFIX 0 C7 1 0.323971 0.031941 0.203141 11.00000 0.04541 0.03048 = 0.04496 -0.00668 -0.00009 0.00504 C8 1 0.364375 0.076154 0.168511 11.00000 0.05406 0.05331 = 0.03911 -0.00882 -0.00238 0.00762 AFIX 43 H8A 2 0.342129 0.062113 0.140109 11.00000 -1.20000 AFIX 0 C9 1 0.436045 0.139514 0.176493 11.00000 0.05558 0.04262 = 0.04356 0.00940 0.00455 0.00737 AFIX 43 H9A 2 0.464845 0.168575 0.153457 11.00000 -1.20000 AFIX 0 C10 1 0.467170 0.161606 0.219502 11.00000 0.04889 0.03175 = 0.04426 0.00210 -0.00292 0.00320 C11 1 0.356534 0.058280 0.245233 11.00000 0.04230 0.03351 = 0.03882 -0.00175 0.00181 0.00605 C12 1 0.312243 0.015569 0.281875 11.00000 0.04005 0.02852 = 0.05065 -0.00218 -0.00031 0.00431 C13 1 0.325792 0.037578 0.402277 11.00000 0.10949 0.05758 = 0.04785 0.01545 -0.00228 -0.00010 AFIX 33 H13A 2 0.372780 0.083395 0.398217 11.00000 -1.50000 H13B 2 0.414885 0.011306 0.418794 11.00000 -1.50000 H13C 2 0.208359 0.039366 0.417594 11.00000 -1.50000 AFIX 0 C14 1 0.550017 0.230916 0.228641 11.00000 0.06592 0.03410 = 0.05159 0.00638 0.00369 -0.00081 AFIX 33 H14A 2 0.559771 0.237450 0.259453 11.00000 -1.50000 H14B 2 0.470613 0.265900 0.216514 11.00000 -1.50000 H14C 2 0.672756 0.233816 0.215813 11.00000 -1.50000 AFIX 0 C28 1 0.207933 0.200126 0.023668 11.00000 0.04711 0.02217 = 0.03790 -0.00178 -0.00214 -0.00228 C29 1 0.191221 0.250617 -0.008927 11.00000 0.04100 0.02593 = 0.03801 -0.00246 0.00007 -0.00038 C30 1 0.186657 0.319766 0.003948 11.00000 0.05111 0.02364 = 0.03864 0.00187 -0.00387 -0.00287 AFIX 43 H30A 2 0.175645 0.353493 -0.017303 11.00000 -1.20000 AFIX 0 C31 1 0.197898 0.339928 0.047097 11.00000 0.05115 0.02168 = 0.03988 -0.00297 0.00118 0.00029 C32 1 0.214418 0.289739 0.079522 11.00000 0.05676 0.02296 = 0.03688 -0.00142 0.00256 -0.00012 C33 1 0.218582 0.221565 0.066726 11.00000 0.05638 0.02599 = 0.03579 0.00295 0.00238 -0.00192 AFIX 43 H33A 2 0.229115 0.188094 0.088150 11.00000 -1.20000 AFIX 0 C34 1 0.228807 0.122797 0.018055 11.00000 0.07091 0.02352 = 0.04674 -0.00120 0.00699 -0.00110 C35 1 0.175625 0.241343 -0.058125 11.00000 0.04974 0.03328 = 0.04043 -0.00367 -0.00258 0.00156 C36 1 0.196697 0.414540 0.059100 11.00000 0.07425 0.02152 = 0.04141 -0.00092 0.00507 0.00295 C37 1 0.237612 0.305872 0.126748 11.00000 0.07004 0.01753 = 0.04093 -0.00049 -0.00183 -0.00418 HKLF 4 1 0.0000 0.0000 1.0000 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 REM KL in Pbca REM R1 = 0.0881 for 2278 Fo > 4sig(Fo) and 0.1489 for all 4346 data REM 316 parameters refined using 3 restraints END WGHT 0.1447 0.0000 REM Highest difference peak 0.368, deepest hole -0.404, 1-sigma level 0.080 Q1 1 0.3190 -0.0004 0.4249 11.00000 0.05 0.37 Q2 1 0.4652 0.2747 0.1315 11.00000 0.05 0.34 Q3 1 0.1872 0.1730 0.0176 11.00000 0.05 0.32 Q4 1 0.0216 0.1224 -0.0773 11.00000 0.05 0.31 Q5 1 0.2384 0.0850 0.4049 11.00000 0.05 0.31 ; _cod_data_source_file lh5664.cif _cod_data_source_block I _cod_database_code 2238889 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity O O1 0.2749(5) 0.08753(12) 0.04898(9) 0.0620(10) Uani d . 1 1 O O1W 0.9045(6) 0.17263(15) 0.15048(10) 0.0773(11) Uani d D 1 1 H H1WA 0.8321 0.1863 0.1316 0.116 Uiso d RD 1 1 H H1WB 0.9732 0.2039 0.1586 0.116 Uiso d RD 1 1 O O2 0.1964(5) 0.09431(13) -0.01923(9) 0.0687(11) Uani d . 1 1 H H2 0.1669 0.1239 -0.0369 0.103 Uiso calc R 1 1 O O3 0.1453(4) 0.18081(12) -0.07332(9) 0.0514(8) Uani d . 1 1 O O4 0.1828(5) 0.29265(13) -0.08131(10) 0.0607(9) Uani d . 1 1 O O5 0.1946(5) 0.45577(12) 0.02561(9) 0.0710(11) Uani d . 1 1 H H5 0.1941 0.4958 0.0340 0.106 Uiso calc R 1 1 O O6 0.1961(6) 0.43455(14) 0.09547(10) 0.0814(12) Uani d . 1 1 O O7 0.1129(5) 0.29909(14) 0.15299(9) 0.0570(9) Uani d . 1 1 O O8 0.4094(5) 0.32175(13) 0.13965(9) 0.0526(8) Uani d . 1 1 H H8 0.4812 0.3203 0.1189 0.079 Uiso calc R 1 1 N N1 0.3348(5) 0.04067(14) 0.32309(11) 0.0418(8) Uani d . 1 1 H H1A 0.3756 0.0820 0.3261 0.050 Uiso calc R 1 1 N N2 0.4269(5) 0.12165(13) 0.25335(10) 0.0387(8) Uani d . 1 1 C C1 0.2968(6) 0.0044(2) 0.35906(14) 0.0505(11) Uani d . 1 1 C C2 0.2298(6) -0.0628(2) 0.35368(16) 0.0565(12) Uani d . 1 1 H H2B 0.2018 -0.0892 0.3780 0.068 Uiso calc R 1 1 C C3 0.2051(6) -0.0901(2) 0.31345(16) 0.0540(12) Uani d . 1 1 H H3A 0.1608 -0.1348 0.3107 0.065 Uiso calc R 1 1 C C4 0.2457(6) -0.05151(18) 0.27592(15) 0.0464(10) Uani d . 1 1 C C5 0.2205(6) -0.07699(19) 0.23280(16) 0.0510(11) Uani d . 1 1 H H5A 0.1792 -0.1218 0.2285 0.061 Uiso calc R 1 1 C C6 0.2559(6) -0.0366(2) 0.19861(16) 0.0498(11) Uani d . 1 1 H H6A 0.2354 -0.0539 0.1709 0.060 Uiso calc R 1 1 C C7 0.3240(6) 0.03194(17) 0.20314(13) 0.0403(9) Uani d . 1 1 C C8 0.3644(6) 0.0762(2) 0.16851(14) 0.0488(10) Uani d . 1 1 H H8A 0.3421 0.0621 0.1401 0.059 Uiso calc R 1 1 C C9 0.4360(6) 0.13951(19) 0.17649(13) 0.0473(10) Uani d . 1 1 H H9A 0.4648 0.1686 0.1535 0.057 Uiso calc R 1 1 C C10 0.4672(6) 0.16161(16) 0.21950(12) 0.0416(10) Uani d . 1 1 C C11 0.3565(5) 0.05828(17) 0.24523(12) 0.0382(9) Uani d . 1 1 C C12 0.3122(5) 0.01557(17) 0.28188(13) 0.0397(10) Uani d . 1 1 C C13 0.3258(8) 0.0376(2) 0.40228(16) 0.0716(15) Uani d . 1 1 H H13A 0.3728 0.0834 0.3982 0.107 Uiso calc R 1 1 H H13B 0.4149 0.0113 0.4188 0.107 Uiso calc R 1 1 H H13C 0.2084 0.0394 0.4176 0.107 Uiso calc R 1 1 C C14 0.5500(6) 0.23092(17) 0.22864(14) 0.0505(11) Uani d . 1 1 H H14A 0.5598 0.2375 0.2595 0.076 Uiso calc R 1 1 H H14B 0.4706 0.2659 0.2165 0.076 Uiso calc R 1 1 H H14C 0.6728 0.2338 0.2158 0.076 Uiso calc R 1 1 C C28 0.2079(5) 0.20013(15) 0.02367(12) 0.0357(9) Uani d . 1 1 C C29 0.1912(5) 0.25062(16) -0.00893(13) 0.0350(9) Uani d . 1 1 C C30 0.1867(5) 0.31977(17) 0.00395(12) 0.0378(9) Uani d . 1 1 H H30A 0.1756 0.3535 -0.0173 0.045 Uiso calc R 1 1 C C31 0.1979(5) 0.33993(16) 0.04710(12) 0.0376(9) Uani d . 1 1 C C32 0.2144(6) 0.28974(16) 0.07952(12) 0.0389(10) Uani d . 1 1 C C33 0.2186(6) 0.22157(17) 0.06673(12) 0.0394(9) Uani d . 1 1 H H33A 0.2291 0.1881 0.0881 0.047 Uiso calc R 1 1 C C34 0.2288(7) 0.12280(18) 0.01805(14) 0.0471(11) Uani d . 1 1 C C35 0.1756(6) 0.24134(18) -0.05812(13) 0.0411(10) Uani d . 1 1 C C36 0.1967(6) 0.41454(17) 0.05910(13) 0.0457(11) Uani d . 1 1 C C37 0.2376(7) 0.30587(16) 0.12675(13) 0.0428(10) Uani d . 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.119(3) 0.0212(13) 0.0460(18) 0.0077(14) -0.0028(17) -0.0004(12) O1W 0.107(3) 0.066(2) 0.058(2) -0.0367(18) -0.023(2) 0.0200(15) O2 0.131(3) 0.0301(14) 0.0452(18) 0.0046(16) -0.0161(18) -0.0095(13) O3 0.077(2) 0.0359(14) 0.0416(17) 0.0044(13) -0.0108(15) -0.0086(12) O4 0.095(3) 0.0408(16) 0.0464(18) -0.0027(14) -0.0044(17) 0.0012(14) O5 0.149(4) 0.0180(13) 0.0458(19) -0.0050(15) -0.0022(19) 0.0033(12) O6 0.171(4) 0.0306(15) 0.0427(19) 0.0046(17) 0.000(2) -0.0069(14) O7 0.075(2) 0.0492(17) 0.0465(18) -0.0069(14) 0.0186(17) -0.0076(13) O8 0.072(2) 0.0489(15) 0.0371(16) -0.0054(14) -0.0002(15) -0.0068(12) N1 0.054(2) 0.0278(15) 0.044(2) 0.0022(14) 0.0008(16) 0.0035(14) N2 0.048(2) 0.0261(14) 0.0421(19) 0.0036(13) -0.0007(16) 0.0003(13) C1 0.057(3) 0.042(2) 0.053(3) 0.0034(19) -0.001(2) 0.0130(19) C2 0.059(3) 0.040(2) 0.071(3) 0.005(2) 0.006(3) 0.022(2) C3 0.052(3) 0.033(2) 0.078(3) 0.0028(18) 0.009(2) 0.009(2) C4 0.043(2) 0.0283(18) 0.068(3) 0.0023(16) 0.001(2) 0.0029(19) C5 0.046(3) 0.030(2) 0.077(3) -0.0055(17) -0.003(2) -0.014(2) C6 0.051(3) 0.043(2) 0.056(3) 0.0024(19) -0.001(2) -0.016(2) C7 0.045(2) 0.0305(19) 0.045(2) 0.0050(15) -0.0001(19) -0.0067(17) C8 0.054(3) 0.053(2) 0.039(2) 0.008(2) -0.002(2) -0.0088(19) C9 0.056(3) 0.043(2) 0.044(2) 0.0074(19) 0.005(2) 0.0094(18) C10 0.049(3) 0.0318(17) 0.044(2) 0.0032(16) -0.0029(19) 0.0021(16) C11 0.042(2) 0.0335(18) 0.039(2) 0.0060(16) 0.0018(18) -0.0017(16) C12 0.040(2) 0.0285(18) 0.051(3) 0.0043(15) -0.0003(19) -0.0022(17) C13 0.109(5) 0.058(3) 0.048(3) 0.000(3) -0.002(3) 0.015(2) C14 0.066(3) 0.034(2) 0.052(3) -0.0008(19) 0.004(2) 0.0064(18) C28 0.047(2) 0.0222(17) 0.038(2) -0.0023(14) -0.0021(17) -0.0018(15) C29 0.041(2) 0.0259(17) 0.038(2) -0.0004(15) 0.0001(17) -0.0025(15) C30 0.051(3) 0.0236(17) 0.039(2) -0.0029(16) -0.0039(18) 0.0019(15) C31 0.051(3) 0.0217(16) 0.040(2) 0.0003(15) 0.0012(18) -0.0030(15) C32 0.057(3) 0.0230(17) 0.037(2) -0.0001(15) 0.0026(18) -0.0014(15) C33 0.056(3) 0.0260(17) 0.036(2) -0.0019(16) 0.0024(19) 0.0029(15) C34 0.071(3) 0.0235(18) 0.047(2) -0.0011(17) 0.007(2) -0.0012(18) C35 0.050(3) 0.033(2) 0.040(2) 0.0016(16) -0.0026(19) -0.0037(17) C36 0.074(3) 0.0215(18) 0.041(2) 0.0029(17) 0.005(2) -0.0009(17) C37 0.070(3) 0.0175(16) 0.041(2) -0.0042(17) -0.002(2) -0.0005(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag H1WA O1W H1WB 110.5 ? C34 O2 H2 109.5 ? C36 O5 H5 109.5 ? C37 O8 H8 109.5 ? C1 N1 C12 123.7(3) n C1 N1 H1A 118.2 ? C12 N1 H1A 118.2 ? C10 N2 C11 117.8(3) n N1 C1 C2 117.5(4) ? N1 C1 C13 118.7(4) ? C2 C1 C13 123.8(4) ? C3 C2 C1 121.0(4) ? C3 C2 H2B 119.5 ? C1 C2 H2B 119.5 ? C2 C3 C4 121.0(4) ? C2 C3 H3A 119.5 ? C4 C3 H3A 119.5 ? C12 C4 C3 117.3(4) ? C12 C4 C5 119.2(4) ? C3 C4 C5 123.6(4) ? C6 C5 C4 120.3(3) ? C6 C5 H5A 119.8 ? C4 C5 H5A 119.8 ? C5 C6 C7 122.4(4) ? C5 C6 H6A 118.8 ? C7 C6 H6A 118.8 ? C8 C7 C11 116.3(3) ? C8 C7 C6 124.7(4) ? C11 C7 C6 119.0(4) ? C9 C8 C7 119.8(4) ? C9 C8 H8A 120.1 ? C7 C8 H8A 120.1 ? C8 C9 C10 120.4(4) ? C8 C9 H9A 119.8 ? C10 C9 H9A 119.8 ? N2 C10 C9 121.6(3) ? N2 C10 C14 117.6(3) ? C9 C10 C14 120.8(3) ? N2 C11 C7 124.1(3) ? N2 C11 C12 117.6(3) ? C7 C11 C12 118.4(3) ? N1 C12 C4 119.6(3) ? N1 C12 C11 119.8(3) ? C4 C12 C11 120.7(4) ? C1 C13 H13A 109.5 ? C1 C13 H13B 109.5 ? H13A C13 H13B 109.5 ? C1 C13 H13C 109.5 ? H13A C13 H13C 109.5 ? H13B C13 H13C 109.5 ? C10 C14 H14A 109.5 ? C10 C14 H14B 109.5 ? H14A C14 H14B 109.5 ? C10 C14 H14C 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? C33 C28 C29 118.3(3) ? C33 C28 C34 113.5(3) ? C29 C28 C34 128.0(3) ? C30 C29 C28 118.0(3) ? C30 C29 C35 113.0(3) ? C28 C29 C35 129.0(3) ? C31 C30 C29 122.7(3) ? C31 C30 H30A 118.6 ? C29 C30 H30A 118.6 ? C30 C31 C32 119.4(3) ? C30 C31 C36 120.7(3) ? C32 C31 C36 120.0(3) ? C33 C32 C31 117.8(3) ? C33 C32 C37 118.4(3) ? C31 C32 C37 123.7(3) ? C32 C33 C28 123.9(3) ? C32 C33 H33A 118.1 ? C28 C33 H33A 118.1 ? O1 C34 O2 120.0(3) ? O1 C34 C28 119.6(3) ? O2 C34 C28 120.4(3) ? O4 C35 O3 122.7(4) ? O4 C35 C29 118.5(3) ? O3 C35 C29 118.7(3) ? O6 C36 O5 123.0(3) ? O6 C36 C31 123.4(3) ? O5 C36 C31 113.6(3) ? O7 C37 O8 120.2(4) ? O7 C37 C32 123.1(4) ? O8 C37 C32 116.3(4) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C34 1.219(5) O1W H1WA 0.8199 O1W H1WB 0.8200 O2 C34 1.296(5) O2 H2 0.8200 O3 C35 1.285(4) O4 C35 1.228(5) O5 C36 1.307(5) O5 H5 0.8200 O6 C36 1.186(5) O7 C37 1.208(5) O8 C37 1.321(5) O8 H8 0.8200 N1 C1 1.341(5) N1 C12 1.369(5) N1 H1A 0.8600 N2 C10 1.331(4) N2 C11 1.354(5) C1 C2 1.401(6) C1 C13 1.494(6) C2 C3 1.359(6) C2 H2B 0.9300 C3 C4 1.408(6) C3 H3A 0.9300 C4 C12 1.400(5) C4 C5 1.429(6) C5 C6 1.337(6) C5 H5A 0.9300 C6 C7 1.426(5) C6 H6A 0.9300 C7 C8 1.400(6) C7 C11 1.413(5) C8 C9 1.356(5) C8 H8A 0.9300 C9 C10 1.410(5) C9 H9A 0.9300 C10 C14 1.498(5) C11 C12 1.436(5) C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 C28 C33 1.392(5) C28 C29 1.409(5) C28 C34 1.521(5) C29 C30 1.403(5) C29 C35 1.530(6) C30 C31 1.388(5) C30 H30A 0.9300 C31 C32 1.402(5) C31 C36 1.498(5) C32 C33 1.384(5) C32 C37 1.497(5) C33 H33A 0.9300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O2 H2 O3 . 0.82 1.58 2.395(4) 170.6 O5 H5 O1 7_665 0.82 1.86 2.671(3) 171.9 O8 H8 O3 3 0.82 1.82 2.645(4) 178.3 N1 H1A O1W 6_556 0.86 1.92 2.738(4) 159.5 O1W H1WA O4 3 0.82 1.92 2.735(4) 170.5 O1W H1WB O7 1_655 0.82 2.11 2.873(4) 155.3 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C12 N1 C1 C2 -0.2(6) C12 N1 C1 C13 -179.6(4) N1 C1 C2 C3 0.2(7) C13 C1 C2 C3 179.6(4) C1 C2 C3 C4 -0.2(7) C2 C3 C4 C12 0.1(6) C2 C3 C4 C5 -179.2(4) C12 C4 C5 C6 -1.6(6) C3 C4 C5 C6 177.7(4) C4 C5 C6 C7 1.7(7) C5 C6 C7 C8 179.6(4) C5 C6 C7 C11 0.4(6) C11 C7 C8 C9 1.9(6) C6 C7 C8 C9 -177.3(4) C7 C8 C9 C10 -1.1(6) C11 N2 C10 C9 0.7(6) C11 N2 C10 C14 -178.3(3) C8 C9 C10 N2 -0.3(6) C8 C9 C10 C14 178.7(4) C10 N2 C11 C7 0.3(6) C10 N2 C11 C12 -179.6(3) C8 C7 C11 N2 -1.6(6) C6 C7 C11 N2 177.7(3) C8 C7 C11 C12 178.3(3) C6 C7 C11 C12 -2.5(6) C1 N1 C12 C4 0.1(6) C1 N1 C12 C11 180.0(3) C3 C4 C12 N1 -0.1(6) C5 C4 C12 N1 179.3(4) C3 C4 C12 C11 -179.9(4) C5 C4 C12 C11 -0.6(6) N2 C11 C12 N1 2.6(5) C7 C11 C12 N1 -177.3(3) N2 C11 C12 C4 -177.6(3) C7 C11 C12 C4 2.5(6) C33 C28 C29 C30 0.1(6) C34 C28 C29 C30 -175.6(4) C33 C28 C29 C35 -179.5(4) C34 C28 C29 C35 4.8(7) C28 C29 C30 C31 0.0(6) C35 C29 C30 C31 179.7(4) C29 C30 C31 C32 0.0(6) C29 C30 C31 C36 178.6(4) C30 C31 C32 C33 -0.1(6) C36 C31 C32 C33 -178.7(4) C30 C31 C32 C37 176.7(4) C36 C31 C32 C37 -2.0(6) C31 C32 C33 C28 0.2(6) C37 C32 C33 C28 -176.7(4) C29 C28 C33 C32 -0.2(6) C34 C28 C33 C32 176.1(4) C33 C28 C34 O1 -8.9(6) C29 C28 C34 O1 167.0(4) C33 C28 C34 O2 170.5(4) C29 C28 C34 O2 -13.6(7) C30 C29 C35 O4 8.2(5) C28 C29 C35 O4 -172.2(4) C30 C29 C35 O3 -168.0(3) C28 C29 C35 O3 11.6(6) C30 C31 C36 O6 175.9(5) C32 C31 C36 O6 -5.4(7) C30 C31 C36 O5 -3.5(6) C32 C31 C36 O5 175.2(4) C33 C32 C37 O7 -77.6(5) C31 C32 C37 O7 105.7(5) C33 C32 C37 O8 95.8(4) C31 C32 C37 O8 -81.0(5) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139086231